Cu(Ⅱ) salen complex catalyzed synthesis of propargylamines by a three-component coupling reaction

doi:10.1016/S1872-2067(12)60683-4

Abstract

Abstract:

A one pot three-component coupling reaction of phenylacetylene, aldehyde, and amine derivatives in the presence of Cu(Ⅱ) Salen complex as an efficient heterogeneous catalyst under solvent-free conditions is reported. The catalyst displayed high activity and afforded the corresponding propargylamines in good to excellent yields. This method provides a wide range of substrate applicability. The catalyst was reused several times without significant loss of its catalytic activity.

Key words: Propargylamine, Salen, Copper, Coupling reaction, Solvent-free

Mahmood Tajbaksh, Maryam Farhang, Hamid Reza Mardani, Rahman Hosseinzadeh, Yaghoub Sarrafi. Cu(Ⅱ) salen complex catalyzed synthesis of propargylamines by a three-component coupling reaction[J]. Chinese Journal of Catalysis, 2013, 34(12): 2217-2222.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(12)60683-4

https://www.cjcatal.com/EN/Y2013/V34/I12/2217

References

[1] Wipf P, Kendall C, Stephenson C R J. J Am Chem Soc, 2001, 123: 5122
[2] Kopka I E, Fataftah Z A, Rathke M W. J Org Chem, 1980, 45: 4616
[3] Imada Y, Yuasa M, Nakamura I, Murahashi S I. J Org Chem, 1994, 59: 2282
[4] Czernecki S, Valéry J M. J Carbohydr Chem, 1990, 9: 767
[5] Murai T, Mutoh Y, Ohta Y, Murakami M. J Am Chem Soc, 2004, 126: 5968
[6] Zani L, Bolm C. Chem Commun, 2006: 4263
[7] Wei C M, Li Z G, Li C J. Org Lett, 2003, 5: 4473
[8] Wei C M, Li C J. J Am Chem Soc, 2003, 125: 9584
[9] Lo V K Y, Liu Y, Wong M K, Che C M. Org Lett, 2006, 8: 1529
[10] Bisai A, Singh V K. Org Lett, 2006, 8: 2405
[11] Sakaguchi S, Mizuta T, Furuwan M, Kubo T, Ishii Y. Chem Commun, 2004: 1638
[12] Li P H, Wang L. Chin J Chem, 2005, 23: 1076
[13] Lee K Y, Lee C G, Na J E, Kim J N. Tetrahedron Lett, 2005, 46: 69
[14] Zhang Y C, Li P H, Wang M, Wang L. J Org Chem, 2009, 74: 4364
[15] Yadav J S, Reddy B V S, Gopal A V H, Patil K S. Tetrahedron Lett, 2009, 50: 3493
[16] Li C J, Wei C M. Chem Commun, 2002: 268
[17] Li Z G, Wei C M, Chen L, Varma R S, Li C J. Tetrahedron Lett, 2004, 45: 2443
[18] Park S B, Alper H. Chem Commun, 2005: 1315
[19] Zhang X, Corma A. Angew Chem Int Ed, 2008, 47: 4358
[20] Reddy K M, Babu N S, Suryanarayana I, Prasad P S S, Lingaiah N. Tetrahedron Lett, 2006, 47: 7563
[21] Wang M, Li P H, Wang L. Eur J Org Chem, 2008: 2255
[22] Kantam M L, Ramani T, Chakrapani L. Synth Commun, 2008, 38: 626
[23] Gupta K C, Kumar Sutar A, Lin C C. Coord Chem Rev, 2009, 253: 1926
[24] Bahramian B, Ardejani F D, Mirkhani V, Badii K. Appl Catal A, 2008, 345: 97
[25] Ribeiro da Silva M D M C, Goncalves J M, Silva A L R, Oliveira P C F C, Schroder B, Ribeiro da Silva M A V. J Mol Catal A, 2004, 224: 207
[26] Karmaker R, Choudhury C R, Bravic G, Sutter J P, Mitra S. Polyhedron, 2004, 23: 949
[27] Moreira C S, Alleoni L R F. Sci Agric, 2010, 67: 301
[28] Eshghi H, Zohuri G H, Damavandi S. Eur J Chem, 2011: 100
[29] Kidwai K, Jahan A. J Iran Chem Soc, 2011, 8: 462
[30] Ramu E, Varala R, Sreelatha N, Adapa S R. Tetrahedron Lett, 2007, 48: 7184
[31] Wang S J, He X X, Song L X, Wang Z Y. Synlett, 2009: 447
[32] Layek K, Chakravarti R, Lakshmi K M, Maheswaran H, Vinu A. Green Chem, 2011, 13: 2878
[33] Ren G R, Zhang J L, Duan Z, Cui M J, Wu Y J. Aust J Chem, 2009, 62: 75
[34] Patil M K, Keller M, Reddy B M, Pale P, Sommer J. Eur J Org Chem, 2008: 4440
[35] Letinois-Halbes U, Pale P, Berger S. J Org Chem, 2005, 70: 9185
[36] Bhatte K D, Sawant D N, Deshmukh K M, Bhanage B M. Catal Commun, 2011, 16: 114
[37] Likhar P R, Roy S, Roy M, Subhas M S, Kantam M L, De R L. Synlett, 2007: 2301
[38] Samai S, Nandi G C, Singh M S. Tetrahedron Lett, 2010, 51: 5555
[39] Lo V K Y, Kung K K Y, Wong M K, Che C M. J Organomet Chem, 2009, 694: 583
[40] Chen W W, Nguyen R V, Li C J. Tetrahedron Lett, 2009, 50: 2895
[41] Sreedhar B, Kumar A S, Reddy P S. Tetrahedron Lett, 2010, 51: 1891
[42] Sharifi A, Mirzaei M, Naimi-Jamal M R. J Chem Res, 2007, 2007: 129